3-Amino-5-methylisoxazole → HCID 58236575, compound

HRID 1026835Notes

Reaction equation

HRID 1026835 reaction equation
[NH2:1][C:2]1[CH:42]=[CH:41][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:40]=[CH:39][C:19]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:18][CH:17]=4)[S:15][C:8]=23)=[C:4]([F:43])[CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:54](Cl)([O:56]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:65][C:66]1[CH:70]=[C:69]([CH3:71])[O:68][N:67]=1>O1CCCC1>[F:43][C:4]1[CH:3]=[C:2]([NH:1][C:54]([NH:65][C:66]2[CH:70]=[C:69]([CH3:71])[O:68][N:67]=2)=[O:56])[CH:42]=[CH:41][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([C:16]3[CH:40]=[CH:39][C:19]([CH2:20][N:21]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[CH:18][CH:17]=3)[S:15][C:8]=12

Participants

6

Reactant 4

HCID 661723-Amino-5-methylisoxazoleHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 58236582HCID 58236582, compound

Product 1

HCID 58236575HCID 58236575, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 366 (0.15 g, 0.25 mmol) and DIPEA (0.11 mL, 0.080 g, 0.61 mmol) in tetrahydrofuran (50 mL) at 0° C. was added triphosgene (0.029 g, 0.098 mmol) and the resulting solution was stirred for 1 h at 0° C. 3-Amino-5-methylisoxazole (0.025 g, 0.25 mmol) was added and the mixture was warmed to room temperature and stirred for 3 h, then quenched with 1 mL of water and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water; the organic phase was collected, washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by silica gel chromatography (eluent 2% MeOH in EtOAc) to give 367 (0.074 g, 4% yield).

Workup

  1. temperaturethe mixture was warmed to room temperature
  2. stirringstirred for 3 h
  3. customquenched with 1 mL of water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate and water
  6. customthe organic phase was collected
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe product was purified by silica gel chromatography (eluent 2% MeOH in EtOAc)

Sources & evidence

ORD record
ord-8b2dea1c90d44d9f92d6c65825498ebe
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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